A group of black painters–nine original members and 17 additional ones–The Florida Highwaymen painted colorful tropical scenes that showcased the beauty of South Florida and the Everglades. The paintings featured bold oranges, yellows, blues, white clouds, and palm trees. “We sold wherever we could, in our cars, on the side of the highway, to beauty salons, and even door-to-door,” says member Isaac Wright. Residents and tourists took a liking to the serene oil paintings and would pay $12 or $25 for one.

The Florida Highwaymen got their start thanks to the ambitious Alfred Hair, a black Ft. Pierce resident who took painting in high school and received training in painting from local white artist A. E. “Bean” Backus. In addition to a knack for painting, Hair wanted to successfully sell the paintings that he and fellow artists were creating.

According to the documentary “The Legends of the Florida Highwaymen,” Hair hired locals in Ft. Pierce to help prep boards and other painting-related material. He focused on quantity, producing as many paintings as possible to make more money. Hair’s brother-in-law, Dr. Carnell Smith Sr, tells Florida Culture that he began by painting backgrounds for the pictures and later “graduated” to painting complete pictures. Some of those who worked with Hair received training from Backus, the local artist. Hair lifted weights so his arms would be stronger and he could paint for a longer period of time, the documentary reports. The group found ways to cut costs by using

Dr. Carnell Smith Sr., one of The Florida Highwaymen.

construction material such as Upson board for painting instead of traditional canvas. Producing 30 to 35 painitings in one day was not outside the norm, says Smith.

Marketing and Making a Name for Themselves

In these days of Web sites to sell the world anything you want or Facebook and Twitter to share your every thought, it may be hard to imagine that selling beautiful artwork would be difficult. But this was the late 1950s and early 1960s in the Deep South, and the painters were black. Galleries didn’t even want to take paintings by black artists. When the Florida Highwaymen went door to door, they would sometimes be the target of racial slurs. Some threatened to call the police on them; others asked where they stole the paintings from.

Mary Ann Carroll, one of The Florida Highwaymen.

Mary Ann Carroll is and was the only female among the group. She had always liked painting, even as a little girl–she saw in her hometown how the painters were buying new cars and finding success. “It was a challenge. You either win or lose,” she says. She trained her children to behave well so she could take them with her. When she started, she had a couple of children; her brood eventually expanded to seven. “I trained them since they were little, and I had no problem carrying them with me,” Carroll told Florida Culture during the recent Floridiana and Highwaymen Artist Show in St. Petersburg.

Desite racial barriers, the artists sold all of their paintings regularly. Sometimes the paint on their paintings was not even dry before they were loading pieces into the car to sell across the state, the documentary reports. “People bought it because it was good looking and cheap,” member Willie Daniels says in the documentary.

The group had a decline when their charismatic leader, Hair, was shot by a fellow patron at a bar in Ft. Pierce in 1970. White and black residents alike of Ft. Pierce turned out for an emotional scene at the hospital after the fight. However, The Florida Highwaymen received renewed attention in 1995 when art agent Jim Fitch wrote an article about their work and gave them their now-famous name Florida Highwaymen. In 2004, they were inducted into the Florida Artists Hall of Fame. Books such as “Florida Highwaymen: Legendary Landscapes,” written by Bob Beatty, have been written about the artists’ traveling past.

The Florida Highwaymen now make appearances at art, antique, and other shows, selling their paintings and sometimes painting on the spot for all to watch. The paintings can now fetch $700 to $8000, says Smith. Original buyers, who let the art they purchased languish in a garage, may not know they are sitting on a piece of Florida culture and history.

Many of the Highwaymen continue to paint either full time or as a hobby. Knight had a 38-year career in the aerospace industry and would paint from 6 p.m. to midnight before during the Highwaymen era, he says. Now that he is retired, he devotes more regular hours to the craft.

Smith is now a minister in the Philadelphia area. He says he paints and makes it to shows when he can “dig out” of the city, joking about the Northeast’s rash of heavy snowstorms this winter.

Buyers are attracted to the paintings because they show a side of Florida that’s going away rapidly, Carroll believes. “It’s in the past, and it will never be seen again. Condos and high rises are pushing it out,” she says.